Abstract: The ubiquity of proprietary technologies embedded within informational modes of pedagogy and research unsettles industrial understandings of privacy and property within educational environments. As educational institutions commit a growing portion of shrinking budgets to proprietary software and outsourced ICT services, their informational infrastructure intertwines with corporations from Google and Blackboard to IBM and Apple. We offer a multi-disciplinary analysis of this proprietary infrastructure, drawing on our respective dissertation research in the fields of Urban Education and Environmental Psychology, to articulate issues of privacy and property experienced by young people and teachers in these educational environments. We begin by summarizing the findings from two independent cases: The MyDigitalFootprint.ORG Project and The NYC Teacher Blog Project. Our first case, MyDigitalFootprint.ORG, is a participatory action design research (PADR) project interested in the concerns of young people developing in proprietary information ecologies. This project began by interviewing young people ages 14-19 in New York City to identify shared online privacy, property, and security concerns. A collective of youth co-researchers was then assembled to further research and take action in response to these concerns through the development of a youth-based open source social network. Through this PADR project, young people participated in investigating and reconfiguring how information is experienced in their everyday environment. Our second case, The NYC Teacher Blog Project, aggregates, stores, and anonymizes the blog posting of New York City teachers for qualitative analysis in order to examine the tension between the realities of everyday pedagogical practices and the tacit privatization of educational policy. Whether at the federal, state, or local levels, teachers’ opinions, local knowledge, and expertise count for naught in the policymaking process as K-12 public school teachers are provided little if any voice in the construction of education policy. The traditional isolation of the teaching environment has provided teachers with little opportunity to connect, reflect, or engage with this process. Yet, as our everyday information infrastructure grows so to do opportunities for teacher expression and research. Blogs have proven an enduring aspect of this infrastructure by providing a space where teachers can reflect, connect, and share local knowledge. We conclude our review of these two cases by discussing strategies for reworking educational boundaries, relationships, and flows towards the privacy, property, and participation concerns of young people and teachers. With the MyDigitalFootprint.ORG Project, we look specifically at the open source software and PADR methods employed to engage young people as producers of social media and participants in social research, rather than as social media consumers and social research subjects. With the NYC Teacher Blog Project, we look specifically at how its partnership with the OpenCUNY Academic Medium, a student-based open source medium at the CUNY Graduate Center, afforded both methodological and epistemological breakthroughs around teacher privacy and property in educational environments.